Since our wedding going to be in Scotland, I'm having only one bridesmaid: his 17 year old sister.
Originally, I found a color we both liked, and we found 3 dresses in that color that we both liked. I told her she could pick whichever she wanted out of the dresses we had chosen. I'm not horribly picky, and I wanted her to feel comfortable and confident as a major figure in my wedding.
However, since she is about the size I was about 10 years ago when I was in high school, I pulled out some of my old dresses and sent them to her. She fell in love with one of them, and asked to wear it for the wedding, which I told her is fine. When I was younger, that particular dress was my absolute favorite piece of clothing...it made me feel like a princess!
The funny thing is, I had always said that I would have a white version of that dress made for myself to use as a wedding dress. Though I'm not doing that now, it's nice to still have that dress be part of my wedding!
Plus, it cuts down on cost!! hee hee.